Wishful Thinking
by Hero in the shadows1
Summary: Time has passed and the Pokémon gang have grown older and added romance to their lives. Some of them anyway, a few haven't found that special someone to be with yet including Ash. But will an old friend break his heart before he can admit his feelings for her or will someone else be there to save him for a change? One sided Pokeshipping, slight Ash/Lily. Three Chapter story.
1. Setting the stage

**Disclaimer: I don't own Pokemon or its affiliates.**

 **A/N: This is an idea that I have had for a while and decided it was time to get out. This is set a few years after the Sinnoh League so that the gang is older. The three older Sensational sisters have stopped using like all the time in this because they have matured out of that phase. Please review and tell me what you liked and disliked, this is my first real try at a romance centered fic so any advice is welcomed.**

 **Ages:**

 **Ash: 20**

 **Misty: 21**

 **Lily: 22**

 **Violet: 23**

 **Daisy: 24**

 **May: 17**

 **Drew: 17**

 **Paul:19**

 **Dawn: 16**

 **Gary: 20**

 **Tracey: 24**

 **Brock: 24**

Cerulean City. A bustling city set near the ocean, famous for it's wondrous array of seafood and the Sensational Sisters of the Cerulean gym. Speaking of the gym, it is abuzz with activity tonight as a party is going on to celebrate a special event that only happens once a year. Misty Waterflower's birthday. The gym had been decked out for the special occasion with streamers, balloons and even a disco ball. The large pool that was usually used for battling was covered and turned into a dance floor where most of the guests were at having a good time dancing to pop music until the birthday girl arrived.

Despite the rain that had been soaking the city for the past week, most of the people who had been invited had shown up, from local friends to the ones who lived in different regions. Among the friends invited a few stood out as best friends, one being a miss May Maple. May was a coordinator from Hoenn who was currently dancing with a friend of hers she had brought with her named Drew Hayden. Both seemed to be enjoying themselves, May in her red silk evening gown and red heels and Drew in a white dress shirt, red bow tie and black dress pants.

Across the room near the punch bowl, a certain blue haired coordinator from Sinnoh named Dawn Berlitz was trying and failing to convince a purple haired boy named Paul Shinji to dance with her. Dawn was wearing a blue strapless dress that went to her knees and blue high heels to make herself taller while Paul was in a simple black dress shirt and black dress pants. Paul had spent the entire time at the party sipping the punch that was provided while glaring at Dawn and any other people who dared look his way. Hearing Dawn rattle on about something, Paul just shook his head and thought to himself."That jerk better show up soon. I only came because he asked me to."

While Dawn was fighting a losing battle with Paul, in another part of the gym three beautiful young ladies were talking with three young men. The three girls were three of the four Sensational Sisters Daisy, Violet and Lily Waterflower while the three men were Tracey Sketchit, Brock Stone and Gary Oak. The oldest of the girls and the blonde of the group, Daisy, was wearing a yellow gown and flat yellow shoes and was talking very intimately with Tracy who was wearing a white dress shirt with a yellow bow tie and black dress pants. Though no one knew about it despite the two's closeness, they had been secretly dating for a few months and seen each other as often as their schedules would allow. They had a few private dinner dates but mostly late night phone calls and text messages were how they stayed in touch with each other. They had decided that they were going to tell everyone about their relationship soon but they both kinda liked the excitement that having a secret relationship can have.

While the secret love birds were chatting the second oldest Waterflower, Violet was chatting with the other two boys Gary and Brock. Violet was wearing a dark blue cocktail dress that matched her hair and dark blue flats while Gary and Brock were wearing white dress shirts and black pants, Gary with a blue bow tie and Brock with a gray one. Brock was busy telling them about how he had graduated from Medical school and was looking for an opening in a Pokemon Center somewhere. While Brock was busy talking, Violet was lightly flirting with him by rubbing his forearm and standing close to him. She had a thing for doctors and thought he was kinda cute in his own way.

Gary was also listening to what Brock was saying but he was more interested watching Violet flirt with Brock and despite his best attempt to convince himself other wise he was a little jealous of Brock. Gary thought Violet was quite beautiful with her blue hair and warm smile plus she cared about her looks, which was something that Gary also prided himself in. After watching as Brock finally noticed Violet flirting with him and start flirting back, Gary had to look away. While scanning around the room he noticed that the third Waterflower sister Lily, who was standing behind her sister was oddly quiet and seemed to be looking around the room for something or someone. Lily was wearing a pink evening gown that went to her feet covering the pink flats that she was wearing. With nothing else to do, Gary decided to figure out what Lily was looking for. "Hey Lily, who you looking for?" Gary asked pleasantly.

Lily jumped in surprise at being questioned while she was in deep concentration before nervously answering Gary. "Oh Gary, you startled me. I wasn't looking for anyone just waiting for the birthday girl and her boyfriend to get here that's all."

Gary eyed her carefully, she was acting like a little kid who had been caught doing something they shouldn't have. Gary already had a high curiosity being a Pokemon professor but Lily's words had only made him even more curious about what she was looking for. "Are you sure that's who you are looking for cause the birthday girl shouldn't be here for another half hour you know." Gary stated with a smirk on his face, knowing he had her cornered.

Alarmed at the fact that she was found out so quickly, Lily stuttered. "Um.. uh well I don't know just looking around I guess." She finished while finding her shoes very interesting.

With a smug chuckle, Gary replied. "OK, OK I won't pry. I was just curious cause you were being so quiet that's all."

"Thanks." Lily whispered, never taking her eyes off her feet.

Seeing that Lily really wasn't up for talking, Gary decided to join Daisy and Tracey's conversation since Brock and Violet were now out on the dance floor, much to his dismay. Shaking off the jealous thoughts, Gary broke into the conversation. "Hey you two, what are you guys talking about?" He said while giving a jealous side ways glance at Brock and Violet who were dancing very close to one another.

Daisy saw the jealous look Gary had given but decided not to comment on it. "Well we were just talking about all the people who are here. There must be fifty or sixty people here."

"Yeah, most of them I don't even know." Tracey spoke up. "A lot of them must be from town but I did notice one very important person is missing. Is Ash going to be here Daisy?"

"I'm not sure, he hasn't called for Misty in almost two months. It's really strange because he used to call about every two weeks or whenever he was at a Pokemon Center. Misty has been pretty upset about it and won't even bring it up anymore. It has been hard on all of us, we always enjoyed hearing all about his adventures." Daisy said sadly.

"Yeah it was amazing to hear about all the people and Pokemon he met and helped." Lily spoke up, suddenly more interested in the conversation.

This didn't go unnoticed by Gary, who had to smirk at finding the truth to his earlier mystery. "So that's who she was looking for." He thought to himself.

"Have you heard anything from Ash, Gary?" Daisy asked, unaware of the sudden change in her sister's mood.

Brought back from his musings about Lily, Gary answered Daisy polity. "No, I haven't heard from him in almost six months. So I probably know less than you guys do about his whereabouts. Last time I talked to him he said he was preparing for something but when I asked what tournament it was he said it didn't have anything to do with Pokemon."

This received a surprised gasp from the other three in the group. Ash Ketchum doing something that didn't involve Pokemon was very unbelievable. Everyone who knew the boy, understood that he was focused on Pokemon and had little time for other things. Sure he had human friends and helped people with their problems but Pokemon were always involved in some way.

Gary knew all this and expected them to react this way and had to chuckle at their shocked faces. "Yeah I know it shocked me too. I wanted to know what had caused this sudden change in my single minded friend but he was being surprisingly secretive about it. All he would say was he needed to improve himself." Gary finished.

The shocked faces around Gary turned to curious ones as Gary finished talking. Daisy was the first to regain her composure and asked what all of them were thinking. "What could he mean by that I wonder?" I mean it's a very vague statement, it could mean any number of thing really."

While everyone else was discussing what Ash had meant, Lily was deep in thought about the boy in question. What did he mean improve himself? Was he changing from who he was and was it for the better? All this worried her greatly, she was worried about him and for him. She had never said a word to anyone about her biggest secret, mostly out of fear of what others may say. Especially Misty who had a crush on Ash for the longest time and Lily couldn't help having the same crush on him. She couldn't help it, when he was around he made her feel like a person unlike the other guys that she had dated. He didn't just look at her for her body but also talked with her when he came to the gym, asked how she was doing and what she had been doing. He would tell her and her sisters the most amazing stories of the adventures he had and the people and Pokemon he had met. It was incredible to hear for someone like Lily who had never been on a Pokemon journey or seen the big, wide world. All this had caused feeling to form in Lily and she felt the need to see Ash more and more, she even started carrying a picture of him in her purse. However now that Misty had a boyfriend, Lily thought that she could at least tell Ash how she felt about him. If he shows up that is.

That was why she was looking for him earlier in the night. Well that and she just wanted to see how much he had matured since she last saw him. But why had he not contacted in the last two months? Was he even coming at all? All this made Lily worry more and more till Gary said something that caught her attention.

"Well speak of the devil and he shall appear." Gary said in surprised tone. "I almost don't recognize him without his hat."

Lily, Tracey and Daisy all turned in the direction that Gary was looking and received a shock. Lily couldn't help but blush at how handsome Ash looked. He was wearing dark blue jeans and black shoes like he always did but these appeared to be new or hardly worn at least. He was also wearing a white button up short sleeve shirt with a white undershirt that fit his well developed chest and arms snugly. The outfit wasn't anything special but Lily was just so used to seeing him in his dirty traveling clothes that this came as a surprise albeit a good one. Something that hadn't changed was the wild mass of black hair that didn't have the usual hat to tame it, giving him a somewhat wild look that Lily liked.

"Wow his appearance sure has changed! Wonder if anything else about him has changed?" Daisy said aloud.

"Yeah, I wonder." Lily said quietly with worry in her voice. Was Ash still the same person she had a crush on or was he a different person now? Had she missed her chance with the Ash she liked?


	2. Complications

**Wishful Thinking**

 **Disclaimer: I don't own Pokemon or it's affiliates.**

 **A/N: I want to apologize for how long this chapter took, I struggled with this chapter a lot. Romance is very difficult for me to write and I decided that this story needs to be longer so I can practice and it allows for more build up in the story. This will now be a three part story and hopefully will be finished in a more timely manner. Thanks for your understanding.**

"Well should we go over and say hi or just stand here staring at him?" Gary asked with a slightly amused tone of voice.

"I don't see why not. You coming Lily?" Daisy asked her younger sister who was still in a daze.

"Uh yeah sure." Lily responded, still unsure from all the questions that were busying her mind.

"Well we better get over there quick. Paul just walked up to Ash and he doesn't look to happy." Gary said while starting toward Ash. Everyone else saw what Gary was talking about and began to quickly make their way through the crowd.

* * *

"Your late Ketchum." Paul said with his usual stern look on his face as he stood in front of Ash with his arms crossed.

"Well hello to you too Paul. Hi Dawn, it's good to see you again." Ash said with a big smile, ignoring Paul's glare.

"Hey Ash it's great to see you too. You sure clean up nice, don't you." Dawn said while giving Ash a once over.

"Gee thanks." Ash spoke while scratching the back of his head in embarrassment. "But I can't take all the credit, my mentor helped pick out the outfit."

"Your mentor? What are you talking about?" Dawn asked curiously.

"So he accepted you as his apprentice?" Paul interrupted.

"Yeah about six months ago actually. It's been the hardest six months of my life too but it should be worth it in the end. I learned so much, not just about my Pokemon but also about myself. It was an incredible experience." Ash explained enthusiastically.

"Seemed like a waste of time to me. You don't seem any different to me." Paul responded curtly.

"Excuse me but what are you two talking about? Who was mentoring you Ash? And what did they teach you?" Dawn asked, slightly irritated at being left out.

At that moment the DJ changed to a new song, a slow song. Ash gained a sly grin and turned to Paul. "I'll show you how different I am." Ash then turned to Dawn and offered his hand. "May I have this dance?"

Surprised by the sudden formal request, Dawn was taken aback for a moment and then shot a quick look at Paul before accepting Ash's hand with a smile. "Yes I would love to dance with you Ash." While holding each others hand Ash lead Dawn out to the dance floor and gave her a little spin that made her giggle before he pulled her in close to him. With no space between them Ash then began to lead Dawn in a waltz around the dance floor that drew the eye of most everyone there.

* * *

"Wow! Who knew Ash could dance." Daisy said with genuine surprise in her voice as she watched Ash and Dawn glide around the dance floor. "He's actually really good, I wonder who taught him?"

"Juan from Sootopolis City." Paul said through clenched teeth. His hands that had been crossed on his chest were now at his sides and balled into fists with both is eyes focused on Ash and Dawn.

"So that's where Ash has been for the last six months, learning to dance?" Gary asked as Lily and Tracey walked up behind him, all eyes on Ash and Dawn. "I knew Ashy boy was slow but it shouldn't take six months to learn to dance."

"Grr! He wasn't just there to learn to dance!" Paul spat angrily at Gary. "Juan was the person who trained Wallace before he became champion remember? Ash was already a decent battler but he lacked in other areas, so Juan educated him." Paul finished with a deep scowl and turned his attention back to Ash and Dawn.

"Geez you don't have to bite my head off!" Gary retorted. "But I wonder why Ash was so secretive about all this?"

"It is strange. Ash is usually a very open person and to keep such a big secret from all of us is very out of character for him." Tracey said with his hand on his chin in thought.

"Maybe he wanted it to be a surprise for someone in particular." Daisy said with a knowing smirk on her face.

"And who would Ash go through all that trouble to surprise?" Gary asked disbelievingly.

"Well he did come back on **Misty's** birthday." Daisy said with an emphasis on Misty's name.

"Oh. Do you think Ashy boy has a thing for Misty?" Gary asked as he pondered the possibility of Daisy's words.

"I think so. They have known each other since they were kids and like I said he used to call every week just to talk to her." Daisy explained as the slow song that was playing ended and Ash and Dawn began to walk over as a hip hop song began to play.

Lily couldn't help the frown that had been on her face for the past few minutes and it had only deepened at what her sister had said. Seeing Ash be so intimately close to another girl had made her more jealous than she would of liked to admit. But the possibility that Ash had learned to dance and Arceus knows what else just for Misty was too much for Lily and she just wanted to cry right there on the spot. She should have known that she never had a chance, she wasn't anything but Misty's sister in Ash's eyes.

"Oh hey guys. Well Paul what did you think?" Ash asked his rival with a smirk as he and Dawn walked up to the group.

"Very impressive Ketchum." Paul answered curtly. As the hip hop song ended another slow song began to play which caused Paul to smirk. Turning to Dawn, Paul bowed quickly and then said in a stiff voice. "Will you dance with me?"

A sly smile came to Dawn's face when Paul asked, almost as if she had expected this reaction. "Sure why not." Dawn answered and took Paul's hand and the two headed for the dance floor.

Ash smirked as Dawn and Paul began to dance. He then turned around to face the group and noticed Lily behind the others with a sad expression on her face. Being who he is, Ash had to see if he could help. "Hey Lily are you okay?"

Looking up and seeing that it was Ash who was the one talking to her, Lily gained a dusting of pink on her cheeks. "Oh hi Ash. Yeah I'm alright, just bored that's all." Lily fibbed.

"Well I can fix that. Would you like to dance with me?"

The frown on Lily's face flipped over into a big smile at Ash's words. "I would love to." Lily replied as she held out her hand toward Ash.

"Alright lets go." Ash said as he took Lily's hand and lead her out to the dance floor.

* * *

Gary had to smirk as he watched Ash and Lily got close to each other and began to dance slowly along with the music. He knew that Lily was enjoying her time with Ash due mostly to the large smile that hadn't been on her face all night until Ash had asked her to dance. It is strange how the heart works, Lily has feelings for Ash while Ash has feelings for Misty and neither one knows how the other feels. Suddenly a thought came to Gary's mind that could ruin a few people's night. "Hey Daisy you know how you said that Ash may like Misty?"

"Yeah why?" Daisy asked, confused at what Gary was getting at.

"Does Ash know that Misty has a boyfriend?" Gary asked hoping beyond hope that his simple friend knew about Misty's relationship. But Gary's hope was dashed as Daisy's face paled and her hand covered her mouth. "Shit! Well someone needs to tell him before Misty and her boyfriend show up. When are they suppose to show up?"

"Right now." Tracey said somberly while pointing to the front door of the Gym where Misty and her boyfriend, Rudy, were standing in slightly damp cloths.

* * *

"Your an amazing dancer Ash." Lily whispered as she and Ash continued to dance with their bodies touching each other.

"Thanks. Your very light on your feet as well." Ash whispered back with a smile. "So now that we are alone are you going to tell me what was wrong earlier?"

Surprise crossed Lily's face at Ash's sudden question but she continued her earlier fib. "Nothing was wrong, I told you that I was just bored."

Ash shook his head with a knowing smirk. "Didn't seem like you were bored to me, seemed more like you were upset about something."

"I. How did?" Lily stuttered in surprise while looking wide eyed at Ash.

"Years of battle have made me very observant, despite what Misty may tell you. So are you going to tell me now what's wrong or do I have to guess?"

Lily bit her lip nervously while thing about what to do. Should she just tell him how much seeing him with another girl bothered her? But if she said that then she would have to explain why it had bothered her and that would mean revealing her secret. Before Lily could come to a decision the music cut out and a familiar voice began to speak over the microphone drawing everyone's attention.

"Hello everyone and welcome to the Cerulean Gym. I want to thank you all for coming to my birthday party and I hope you are all having a good time." Misty stopped because of the loud cheer that rang out and while she was paused Rudy leaned over and whispered in her ear causing her to blush and shake her head yes. "Since I have all of you here, I have an announcement to make. Most of you know that I have been dating Rudy for a few months now."

At this Ash gained a shocked expression and looked to Lily for answers. All Lily could do was give a sympathetic look in return as Misty continued.

"And things have been going spectacularly. We both make each other very happy, so happy that we decided to take things to the next step."

Ash's face paled and his shoulders were tense. Hoping to calm Ash, Lily reached out and took one of his hands in both of hers.

"Earlier tonight Rudy asked me to marry him and I said yes!" Misty exclaimed excitedly while holding up her left hand to show the engagement ring on her ring finger.

While most of the crowd gave a loud applause and cheered for the happy couple, there were a few who were less excited than the rest. While the small group did clap for Misty and Rudy's happiness, all their eyes were focused on someone else. A certain raven haired young man who hadn't made a move since Misty finished.


	3. Conclusion

**Chapter 3**

 **Disclaimer: I don't own Pokemon or it's affiliates.**

 **A/N: I want to thank all of you who have been patient with me with this story and my others. I have had a bad case of writers block and this story in particular was the cause. Those who are familiar with my first story know that romance is not my thing, I have an extremely hard time writing it and making it come out the way that I want it to. That being said, I originally started this story to practice writing romance because I wanted to improve before I started my Gym Leader story that I promised I would write. This project evolved into more than that but it was a slow go of things and I hope it is a satisfying ending. Again sorry for the long wait and please review or PM me your thoughts on this, any advice would be much appreciated.**

"Come on Ash. What are you going to do?" Gary muttered in a low voice but Daisy still heard him even over the excited crowd.

"You don't think he will do something crazy do you Gary?" Daisy asked while looking toward Ash with a sympathetic expression.

Still watching Ash through the bustling crowd, Gary replied to Daisy's question. "Honestly I don't know. But it would probably be best if you go congratulate your little sister, she did just get engaged after all. I'll keep an eye on Ash okay."

Seeing the seriousness on Gary's face, Daisy could tell that he was uncertain if he could keep his word about Ash but she knew he was right about her sister. "Alright. Come on Tracey lets go."

Nodding Tracey took daisy's hand and they headed to the DJ stand where Misty and Rudy were standing with a crowd of people congratulating them. Gary glanced at them as they left but quickly went back to Ash and Lily. Lily was holding one of Ash's hands in both of hers but Ash's stone faced expression didn't give the impression that he noticed. Gary couldn't help but feel sorry for his friend and former rival. Despite having dated many different women in his short life, Gary had never known them for very long or developed deep feelings for them like Ash apparently had for Misty. Not knowing what Ash may be feeling made it a guessing game of what Ash would do now and how to help him.

The guessing was cut short however when Rudy pulled Misty in for a passionate kiss that drew oh's from most everyone watching. Gary saw the kiss but immediately turned to see Ash backing away from the scene with Lily trying to stop him. After a few steps Ash turned and began to quickly push his way thru the crowd to the back door of the gym and out into the rain.

"Ash wait!" Gary heard Lily cry out over the crowd as she tried to follow him.

"Damn it Ash, don't do anything stupid." Gary mumbled to himself as he made his way through the crowd of dancing couples to where his friend had gone.

* * *

"Stupid, stupid, stupid! How could I be so stupid!" Ash ranted angrily while pulling at his soaking wet hair as he paced back and forth across the gym's backyard. The backyard was typical of a city home but since the gym was so large it was twice as wide as a normal one. Despite the extra size there was very little in the yard besides a few shade trees and three lounge chairs that the Sensational Sisters used for sun bathing. "Argh! Damn it!" Ash cried as he sat on the end of one of the lounge chairs with his head in his hands.

"Ash are you okay?" A familiar soft voice spoke through the rain.

Slowly looking up, Ash saw a now soaking wet Lily standing by him, looking genuinely concerned. "No I'm not. How could she not tell me about this, I thought we were friends!" Ash spat.

"Misty is your friend Ash. You two have been friends for years and that won't change, you know that." Lily explained. "I'm sure she had her reasons for not telling you about Rudy."

Standing silently behind a tree near the back door, Gary listened intently tot he conversation that was taking place.

"And what would that be?! What reason would she have for not telling me?!" Ash said angrily as he stood up from the chair and turned his back to Lily.

"Maybe she just didn't want to hurt you." Lily said quietly. "She cares about you a lot, probably more than you realize."

Ash was silent for a moment as he let her words sink in before he spoke in a softer voice. "And I care about her a lot too. That's why I was gone for so long, I wanted to make myself better for her. But now I come back and she's with him, seeing them together like that and how happy they are. What do I do now?"

Lily walked up next to Ash and put her hand on his shoulder. "You made yourself better for her right?" Seeing Ash's small nod Lily continued. "But you were perfect just being you, you didn't have to change for anyone Ash. If you wanted to better yourself you should do it for you and no one else."

Turning his head to look at Lily, Ash saw that she was smiling at him. Seeing her smile he couldn't help but gain a small grin. "Yeah maybe your right but it doesn't make this hurt any less."

Shuffling her feet nervously, Lily decided to say something that was on her chest. "Ash if you could have told Misty how you felt about her before, would you have?"

"In a heartbeat. I never want to miss out on something just because I'm scared or think I'm not good enough. Life's too short." Ash said with a smile as the rain continued to fall on the pair.

"I agree completely and that's why I want you to know that Misty's not the only one around here that cares about you."

"What do you..." Ash started but was cut off by a pair of soft lips pressed against his. A soft tingling seemed to go through Ash's body as the pair of lips touched his own and then they both were gone.

"I care about you ash and I wanted you to know that before it was too late." Lily said with a smile as she turned and ran to the back door leaving a dumbfounded Ash out in the rain.

Touching his lips, Ash couldn't feel the tingle anymore but he remembered how amazing it had felt on his lips and through his whole body. It was completely different from the shocks Pikachu gave him, more a pleasant feeling that he couldn't describe than a painful one.

"It's an amazing feeling isn't it? First kisses are always special Ashy boy."

"Gary? Were you spying on us?" Ash replied.

"No, not spying. Just making sure you didn't do something stupid but I guess Lily had everything under control." Gary said with a smirk.

"Yeah I guess." Ash said with a small grin.

"So what are you going to do now?"

"What do you mean?" Ash asked with a curious expression while looking at Gary.

"Heh somethings never change." Gary said as he stepped toward Ash. "The way I see it you have two choices. One you can leave now and deal with all this when you have cleared your head and there's not so many people around."

"And whats the other choice?" Ash asked as lightning flashed across the sky.

"Well I can almost guarantee that a certain pink haired women wouldn't object if you asked her to dance again. After that it's up to you." Gary spoke confidently with his arms crossed.

A big smile came across Ash's face. "Well come on we don't want to keep the lady waiting." Ash said as the two friends headed back into the party. Because life is too short.

The End?


End file.
